N-bromobutanimide → Tert-butyl 5-(bromomethyl)-2-phenylthiazole-4-carboxylate

HRID 453286Notes

Reaction equation

HRID 453286 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].[Br:20]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:20][CH2:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 67424508Tert-butyl 5-methyl-2-phenylthiazole-4-carboxylate

Product 1

HCID 67424804Tert-butyl 5-(bromomethyl)-2-phenylthiazole-4-carboxylateYield 75%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of tert-butyl 5-methyl-2-phenylthiazole-4-carboxylate (1.0 g. 3.64 mmol), N-bromosuccinimide (NBS) (0.65 g 3.64 mmol), and benzoyl peroxide (BPO) (5.5 mg, 0.023 mmol) in CCl4 (30 ml) was heated at reflux for 16 h. The reaction mixture was concentrated in vacuo and purified by flash chromatography to give tert-butyl 5-(bromomethyl)-2-phenylthiazole-4-carboxylate as a light yellow solid (0.96 g, 75% yield).

Workup

  1. temperatureat reflux for 16 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. custompurified by flash chromatography

Sources & evidence

ORD record
ord-c0d931a190b44efa8c854b82319954b1
Source dataset
uspto-grants-2013_07
Patent number
US08492401B2

Reaction notes

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